Benzothiadiazine compounds

ABSTRACT

New and valuable substituted 2,1,3-benzothiadiazine compounds having a herbicidal action, herbicides containing these compounds as active ingredients, proceses for controlling the growth of unwanted plants with these compounds, and methods of manufacturing them.

The present invention relates to new and valuable substituted 2,1,3-benzothiadiazine compounds having a herbicidal action, herbicides containing these compounds as active ingredients, processes for controlling the growth of unwanted plants with these compounds, and methods of manufacturing them.

It is known that 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide has a selective herbicidal action (German Pat. No. 1,542,836). Other herbicides from this class of compounds are also known which may be used for removing unwanted plants from a number of crop plants (German Laid-Open Applications DOS Nos. 2,444,383; 2,443,901; and 2,458,343).

We have now found that compounds of the formula ##STR1## where R¹ and R² are identical or different and each denotes alkyl, cycloalkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxycarboalkyl, alkoxycarboalkenyl, dialkylketone, azidoalkyl, thiocyanatoalkyl, cyanoalkyl, benzyl, unsubstituted or substituted carbamidoalkyl, unsubstituted or halo- or methyl-substituted aryl, and the following radicals, the final alkyl in each case having more than 1 carbon atom; unsubstituted or substituted haloalkyl or alkylmercaptoalkyl, arylmercaptoalkyl and alkoxyalkyl; R¹ further denotes hydroxyalkyl having more than 1 carbon atom or methyl substituted by O-alkyl-N-alkylaminophosphorothio, O,O-dialkylphosphoro, O,O,O-trialkylphosphinylimino, alkoxydithiocarbonyl, alkoxycarbamoyl, alkoxycarbamoyl-N-aryl, alkylsulfinyl, alkylsulfonyl, thiocarbamido, isothiuronium hydrochloride, ##STR2## or unsubstituted or substituted acylamido, diacylamido or isoxazole; each X independently denotes halogen, --NO₂, lower alkyl, halogen lower alkyl, cycloalkyl, aryl, --SCN, --CN, --CO₂ R³, ##STR3## --Y"R⁴, --SO₂ R³, --SO₂ OR³, ##STR4## --CCl₃, --CF₃, --CH₂ --O--CH₃, ##STR5## or --Y'--CF₂ C(Z)₃, m denotes one of the integers 0, 1, 2, 3 and 4 an n denotes one of the integers 1 and 2, R³ denoting lower alkyl, R⁴ denoting lower alkyl or hydrogen, R⁵ denoting lower alkyl or aryl, each Y, Y' and Y" independently denoting oxygen or sulfur, and each Z independently denoting hydrogen, fluoro, bromo or chloro, enable unwanted broadleaved plants and Cyperaceae to be controlled beyond the known range for this class of compounds, in more crops and with much less risk than was hitherto the case.

The compounds according to the invention have better solubility in nonpolar hydrocarbons, e.g., vegetable or animal oils, and therefore offer technological advantages in the manufacture and application of the compounds as herbicidal agents. The compounds of the invention are thus a considerable enrichment of the art.

The new benzothiadiazine compounds are obtained by reacting 2,1,3-benzothiadiazine compounds of the formula ##STR6## where R², Y, X, m and n have the above meanings, with

(a) a halogen compound of the formula

    Hal--R.sup.1                                               II,

where R¹ has the above meanings and Hal denotes a halogen atom, or

(b) a sulfate of the formula

    SO.sub.2 (OR.sup.1).sub.2                                  III,

or

(c) a sulfone ester of the formula

    ArSO.sub.2 OR.sup.1                                        IV,

where R¹ has the above meanings and Ar denotes aryl, in the presence or absence of an acid binder and of a solvent, or by reacting salts of compounds of the formula I with a halogen compound of the formula II or a sulfate of the formula III or a sulfone ester of the formula IV in the presence of a solvent, or by reacting benzothiadiazine compounds of the formula ##STR7## where R², Y, X, m and n have the above meanings and Hal denotes a halogen atom, with a salt of hydrocyanic acid, thiocyanic acid, hydrazoic acid, unsubstituted or substituted carbamic or thiocarbamic acid, alkoxydithiocarbamic acid, O-alkyl-N-alkylaminothiophosphoric acid, an O,O,O-trialkylphosphite or thiourea, or by reacting compounds of the formula ##STR8## where R², Y, X, m and n have the above meanings, with an isocyanate of the formula

    O═C═N--R.sup.5                                     VII,

where R⁵ denotes lower alkyl or phenyl.

The reaction of starting compounds I and II is preferred.

Examples of meanings for R¹ and R² are methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tertbutyl, cyclobutyl, n-pentyl, 2-pentyl, 3-pentyl, tert-amyl, neopentyl, 2-methylbutyl, 3-methylbutyl, 3-methyl-2-butyl, cyclopentyl, n-hexyl, 4-methyl-2-pentyl, 2,3-dimethylbutyl, 2-methyl-1-pentyl, 2-hexyl, 3-methyl-2-pentyl, 3-methylpentyl, 4-methylpentyl, 3-methyl-3-pentyl, 4,4-dimethylbutyl, cyclohexyl, heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-octyl, 2-octyl, 3-octyl, 4-octyl, 5-octyl, 5-ethyl-2-heptyl, 2,6-dimethyl-4-heptyl, 7-ethyl-2-methyl-4-nonyl, 2,4-dimethyl-3-pentyl, 3-methyl-2-heptyl, 5-ethyl-2-nonyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 6-ethyl-3-decyl, 6-ethyl-3-octyl, 2-methyl-2-pentyl, 2,3-dimethyl-2-butyl, 2-methyl-2-hexyl, 3-ethyl-3-pentyl, 3-methyl-3-hexyl, 2,3-dimethylpentyl-3, 2,4-dimethyl-2-pentyl, 2,2,3-trimethyl-3-butyl, 2-methyl-2-heptyl, 4-methyl-4-heptyl, 2,4-dimethyl-2-hexyl, 2-methyl-2-octyl, 1-methyl-1-cyclopentyl, 1-methyl-1-cyclohexyl, 1-ethyl-1-cyclohexyl, chlorotert-butyl, 1,1-dichloro-2-methyl-2-propyl, 1,3-dichloro-2-methyl-2-propyl, 1-cyclohexyl-1-ethyl, 1-chloroethyl, 2-chloroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1-chloro-2-propyl, 2-chlorobutyl, 2-chloro-2-methyl-3-propyl, 1-fluoroethyl, 2-fluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 1-fluoro-2-propyl, 2-fluorobutyl, 2-fluoro-2-methyl-3-propyl, 2-bromoethyl, 3-bromopropyl, 4-chlorobutyl, 2-chlorocyclohexyl, 1,1,1-trifluoroisopropyl, hexafluoro-2-methylisopropyl, hexafluoroisopropyl, hexachloroisopropyl, 1,2-dibromallyl, 2,2,2-trifluoroethyl, 1-chlorobutyn-2-yl-4, 3-chlorobutyn-1-yl-4, 1-chlorobuten-2-yl-4, 2,2,2-trichloroethyl, 1-chloropentyn-2-yl-4, 2,2,2-tribromoethyl, 3,4,4-trichlorobuten-3-yl-2, 1-bromo-2-propyl, 1,3-dibromo-2-propyl, 3-chlorobuten-1-yl-4, benzyl, o,m,p-toluene, o,m,p-fluorophenyl, vinyl, ethynyl, propen-1-yl, propyn-1-yl, allyl, propargyl, crotyl, butyn-2-yl-1, methallyl, buten-1-yl-3, butyn-1-yl-3, buten-1-yl-4, 2-methylbuten-1-yl-3, 2-methylbuten-2-yl-1, 2-methylbuten-2-yl-4, 3-methylbuten-1-yl-3, 3-methylbutyn-1-yl-3, 2-methylbuten-1-yl-4, 2-ethylhexen-2-yl-1, hexen-5-yl-1, undecen-10-yl-1, 1-ethynylcyclohexyl, methoxyethyl, ethoxyethyl, 3-methoxypropyl, methoxyisopropyl, 3-methoxybutyl, 1-methoxybutyl-2, ethoxy-tert-butyl, methoxy-tert-butyl, cyclohexoxy-tert-butyl, 2-methoxybutyl, 4-methoxybutyl, β-methylmercaptoethyl, β-ethylmercaptoethyl, 3-methylmercaptopropyl, 3-methylmercaptobutyl, 1-methylmercaptobutyl-2, methylmercapto-tert-butyl, 2-methylmercaptobutyl, 4-methylmercaptobutyl, 3-n-butoxyethyl, 2-ethoxypropyl, 3-ethoxy-2-propyl, 2-methylbutanon-2-yl-2, 2-methylpentanon-4-yl-2, 3-butanon-1-yl, 3-butanon-2-yl, 2-propanon-1-yl, 2-pentanon-1-yl, methyl acetate-2, ethyl acetate-2, methyl propionate-2, methyl propionate-3, methyl butyrate-2, methyl butyrate-3, methyl butyrate-4, methyl-(2-vinylpropionate-2), methyl-(2-vinylacetate-2), methylcarbamoylmethyl, dimethylcarbamoylmethyl, carbamoylmethyl, carbamoylethyl, α-cyanoethyl, β-cyanoethyl, γ-cyanoethyl, and β-pheylmercaptoethyl.

R¹ may also denote cyanomethyl, thiocyanomethyl, azidomethyl, dimethylcarbamoylthiomethyl, dimethyldithiocarbamoylmethyl, diethylcarbamoylthiomethyl, diethyldithiocarbamoylmethyl, diisopropyldithiocarbamoylmethyl, diisobutylcarbamoylthiomethyl, hexamethylenecarbamoylthiomethyl, N-ethyl-N-butylcarbamoylthiomethyl, N-ethyl-N-butyldithiocarbamoylmethyl, 2-methylhexahydroazepinecarbodithiomethyl, 2,4,4-trimethylazetidinecarbithiomethyl, 2,4,4-trimethylazetidinecarbodithiomethyl, chloroacetoamidomethyl, phthalyliminomethyl, phenylcarbamoyloxymethyl, O-ethyl-N-isopropylaminophosphorothiomethyl, methylsulfynylmethyl, ethylsulfynylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl, 3-methylisoxazole-5-methyl, 3-methyl-4-chloroisoxazole-5-methyl, O,O-dimethylphosphoromethyl, O,O-diethylphosphoromethyl, thiocarbamidomethyl, methoxycarbamoyl-N-phenylmethyl, ethoxycarbamoylmethyl, p-fluorophenylcarbamoyloxymethyl, diisobutylcarbamoylthiomethyl, ethoxydithiocarbonylmethyl, isothiuronium hydrochloride methyl, O,O,O-triethylphosphynyliminomethyl, and the radicals β-hydroxyethyl, α-acetamido-β,β,β-trichloroethyl, α-formamido-β,β,β-trichloroethyl, α-[α-methoxycarbomethylthio]-acetic acid methyl ester, α-ethoxycarbamidoacetic acid, β,β,β-trichloroethyl-α-acetic acid.

The term "halogen" denotes fluorine, chlorine, bromine and iodine. The terms "lower alkyl" and "halogen lower alkyl" denote linear or branched, unsubstituted or halogen-substituted alkyl of from 1 to 6 carbon atoms.

The term "cycloalkyl" denotes for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. The term "aryl" denotes phenyl and substituted phenyl such as halophenyl or tolyl.

If the starting materials are the sodium salt of 3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and butynyl chloride, the reaction may be represented by the following scheme: ##STR9##

If the starting materials are 3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and dimethyl sulfate (b) or methyl p-toluenesulfonate (c), the reaction is represented by the following schemes: ##STR10##

If the starting materials are 1-chloromethyl-3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and the dimethylammonium salt of dimethyldithiocarbamic acid, the reaction is represented by the following scheme: ##STR11##

If the starting materials are 1-methylol-3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2,-dioxide and phenyl isocyanate, the reaction may be represented by the following scheme: ##STR12##

In a preferred embodiment of methods a, b and c according to the invention, a 2,1,3-benzothiadiazin-(4)-one-2,2-dioxide or a salt thereof is reacted with a halogen compound, an alkyl sulfate or a sulfone ester in the presence or absence of an inert solvent and of an acid binder at a temperature of from -30° to +150° C., preferably from +10° to +90° C., for from 10 minutes to 6 hours, at atmospheric or superatmospheric pressure, and continuously or batchwise.

In method d according to the invention, for instance a compound of the formula V is reacted with a salt of O-alkyl-N-alkylaminothiophosphoric acid, hydrocyanic acid, thiocyanic acid, hydrazoic acid, ethoxydithiocarbamic acid or of an unsubstituted or substituted carbamic or thiocarbamic acid, or with an O,O,O-trialkylphosphite or thiourea, in the presence or absence of a solvent and of an acid binder at a temperature of from -30° to +150° C., preferably from +10° to +90° C., for from 10 minutes to 6 hours, at atmospheric or superatmospheric pressure, and continuously or batchwise.

In method e according to the invention, for instance a compound of the formula VI is reacted with an isocyanate of the formula VII in the presence or absence of a solvent at a temperature of from -30° to +150° C., preferably from +10° to +90° C., for from 30 minutes to 6 hours, at atmospheric or superatmospheric pressure, and continuously or batchwise.

Preferred inert solvents in the processes according to the invention include hydrocarbons such as ligroin, benzene fractions, e.g., those within a boiling range of from 70° to 140° C., cyclohexane, pentane, hexane, petroleum ether, and o-, m- and p-xylene; nitrohydrocarbons such as nitrobenzene and nitroethane; nitriles such as acetonitrile, butyronitrile and isobutyronitrile; ethers such as diethyl ether, di-n-propyl ether, tetrahydrofuran, dioxane and anisole; esters such as acetoacetic ester, ethyl acetate, isobutyl acetate, methyl benzoate and phenyl acetate; amides such as formamide, methylformamide and dimethylformamide; and ketones such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone. If the compounds of the formula I or VI (and not their salts) are used, halohydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,1- and 1,2-dichloroethane, 1,1,1- and 1,1,2-trichloroethane, chlorobenzene, o-, m- and p-dichlorobenzene and o-, m- and p-chlorotoluene are also preferred solvents. If the salts of compounds of the formula I are used, water is also a preferred solvent in methods a, b and c. As acid binder, any of the agents conventionally used for this purpose may be employed. Preferred examples are alkali metal hydroxides, alkali metal carbonates and tertiary organic bases. Particularly suitable compounds are sodium hydroxide, sodium carbonate, sodium bicarbonate, triethylamine, pyridine, trimethylamine, α-, β- and γ-picoline, lutidine, N,N-dimethylaniline, N,N-dimethylcyclohexylamine, quinoline, tri-n-propylamine, n-propyldiisopropylamine and tri-n-butylamine.

In addition to starting materials I, their alkali metal, alkaline earth metal or ammonium salts may also be advantageously used as starting materials. The compounds of the formulae I, V and VI used as starting materials are advantageously employed in an amount of from 0.3 to 1, preferably 0.8 to 1, mole per mole of starting material II, III, IV or VII.

The starting materials may be added in any order. The following procedure is particularly preferred. A solution of starting materials II, III or IV in one of the abovementioned inert solvents is run into a solution or suspension of starting material I, or salt thereof, in one of the abovementioned inert solvents; alternatively, a solution or a suspension of a salt of O-alkyl-N-alkylaminothiophosphoric, hydrocyanic, thiocyanic, hydrazoic, alkoxydithiocarbamic or a substituted or unsubstituted carbamic or thiocarbamic acid, or of an O,O,O-trialkylphosphite or of thiourea in one of the abovementioned inert solvents is run into a solution of starting material V; alternatively, a solution of starting material VII in one of the abovementioned solvents is run into a solution of starting material VI. The reaction is then carried out in the abovementioned temperature range.

To accelerate the reaction of starting materials I with fluorine or chlorine compounds of the formula II, an alkali metal or alkaline earth metal salt of a heavy halogen atom, e.g., sodium or calcium iodide, may be added as catalyst. If a two-phase solvent system is used, quaternary ammonium compounds are also suitable as catalyst. The amount of catalysts to be used in accordance with the invention is from 0.1 to 10 wt%, based on starting material II. To isolate the compounds of the formula VIII from the reaction mixture in methods a to e of the invention, the reaction mixture is stirred--when solvents miscible with water are used--into a dilute aqueous alkaline solution. The oil which separates out is if desired extracted, washed with water and dried. If the solvent is only slightly polar and immiscible with water, the reaction solution may also be extracted direct with a dilute aqueous alkaline solution and water. If desired, the reaction mixture may also be preconcentrated, taken up in a solvent immiscible with water, and purified as described above. The desired end products are obtained by drying and concentrating the organic phase. If desired, they may be further purified in conventional manner, e.g., by recrystallization or chromatography.

EXAMPLE 1

At 22° C. and while stirring, 22.8 parts of methyl chloroacetate was introduced over a period of 10 minutes into a solution of 52.4 parts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide-1-sodium salt in 200 parts of acetone. After stirring for 1 hour at 50° C., the reaction mixture was concentrated in vacuo, taken up in 250 parts of methylene chloride and extracted 3 times with 100 ml of 0.5 N caustic soda solution and with water. After drying over magnesium sulfate and concentration in vacuo, 1-methylcarbomethoxy-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was obtained in the form of colorless crystals; m.p.: 93°-96° C.

EXAMPLE 2

While stirring and at 24° C., 25.3 parts of 1-chlorobutyne-3 was dripped over a period of 10 minutes into a solution of 1 part of sodium iodide and 80 parts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide-1-potassium salt in 630 parts of acetonitrile. After the reaction mixture had been stirred for 10 hours at 82° C., it was concentrated in vacuo, taken up in 300 parts of methylene chloride, extracted four times with 0.5 N caustic soda solution, each time with 100 ml, and extracted with water. After drying over magnesium sulfate, chormatographing using neutral aluminum oxide and concentration in vacuo, 1-butyn-(3')-yl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was isolated in the form of colorless crystals; m.p.: 66°-70° C.

EXAMPLE 3

At 10° C. and while stirring, 16.5 parts of diethyl sulfate was introduced over a period of 15 minutes into a solution of 24 parts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and 4.5 parts of sodium hydroxide in 25 parts of water. The reaction mixture was then stirred for 10 hours at 20° C., 150 parts of 1,2-dichloroethane was added, and the resultant mixture was extracted twice with 0.5 N caustic soda solution, each time in an amount of 70 ml, and with water. After drying, concentration in vacuo and trituration with cyclohexane, 1-ethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was isolated in the form of colorless crystals; m.p.: 56°-58° C.

EXAMPLE 4

At 10° C. and while stirring, a solution of 16 parts of the dimethylammonium salt of O-ethyl-N-isopropylaminothiophosphoric acid in 60 parts of acetonitrile was introduced over a period of 10 minutes into a solution of 20.2 parts of 1-chloromethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide in 160 parts of acetonitrile. The reaction mixture was then stirred for 2 hours at 25° C., concentrated in vacuo, taken up in 200 parts of diethyl ether, and extracted 3 times with a 10% sodium bicarbonate solution, each time with 100 parts, and with water. After drying over magnesium sulfate, concentration in vacuo and trituration with cyclohexane, 1-methyl(O-ethyl-N-isopropylaminophosphorothio)-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was obtained in the form of colorless crystals; m.p.: 79°-84° C.

EXAMPLE 5

100 parts of 1-chloromethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and 150 parts of sodium azide were stirred in 800 parts of dimethylformamide for 6 hours at 25° C. The suspension was then diluted with 5 times its volume of water. After 1 hour, the precipitated crystals were suction filtered and dried. There was obtained 100 parts (98% of theory) of 1-azidomethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide; m.p.: 83° C.

Further active ingredients corresponding to the general formula were prepared by analogous methods. They are listed in Table I, m denoting O.

                                      TABLE 1                                      __________________________________________________________________________     R.sup.1         R.sup.2        Y   n   m.p. (°C.)                       __________________________________________________________________________     C.sub.2 H.sub.5 CH.sub.3       O   2                                           n-C.sub.3 H.sub.7                                                                              CH.sub.3       O   2   39                                      i-C.sub.3 H.sub.7                                                                              CH.sub.3       O   2                                            ##STR13##      CH.sub.3       O   2                                           n-C.sub.4 H.sub.9                                                                              CH.sub.3       O   2                                           CH.sub.3        CH.sub.3       S   2                                           CH.sub.3        CH.sub.3       O   1                                           i-C.sub.3 H.sub.7                                                                              CH.sub.3       O   1                                           i-C.sub.3 H.sub.7                                                                              CH.sub.3       S   1                                           i-C.sub.4 H.sub.9                                                                              CH.sub.3       O   2                                           sec-C.sub.4 H.sub.9                                                                            CH.sub.3       O   2                                           tert-C.sub.4 H.sub.9                                                                           CH.sub.3       O   2                                           CH.sub.3        C.sub.2 H.sub.5                                                                               O   2                                           C.sub.2 H.sub.5 C.sub.2 H.sub.5                                                                               O   2                                           C.sub.2 H.sub.5 C.sub.2 H.sub.5                                                                               O   1                                           n-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                                                               O   2                                           n-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                                                               S   2                                           i-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                                                               O   2                                            ##STR14##      C.sub.2 H.sub.5                                                                               O   2                                           n-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                                                               O   2                                           sec-C.sub.4 H.sub.9                                                                            C.sub.2 H.sub.5                                                                               O   2                                           i-C.sub.4 H.sub.9                                                                              C.sub.2 H.sub.5                                                                               O   2                                           tert-C.sub.4 H.sub.9                                                                           C.sub.2 H.sub.5                                                                               O   2                                           i-C.sub.3 H.sub.7                                                                              C.sub.2 H.sub.5                                                                               S   2                                           CH.sub.3        n-C.sub.3 H.sub.7                                                                             O   2                                           C.sub.2 H.sub.5 n-C.sub.3 H.sub.7                                                                             O   2                                           i-C.sub.3 H.sub.7                                                                              n-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.3 H.sub.7                                                                              n-C.sub.3 H.sub.7                                                                             O   2                                           i-C.sub.3 H.sub.7                                                                              n-C.sub.3 H.sub.7                                                                             O   1                                           n-C.sub.4 H.sub.9                                                                              n-C.sub.3 H.sub.7                                                                             O   2                                           i-C.sub.4 H.sub.9                                                                              n-C.sub.3 H.sub.7                                                                             O   2                                           sec-C.sub.4 H.sub.9                                                                            n-C.sub.3 H.sub.7                                                                             O   2                                           tert-C.sub.4 H.sub.9                                                                           n-C.sub.3 H.sub.7                                                                             O   2                                           C.sub.2 H.sub.5 n-C.sub.3 H.sub.7                                                                             S   2                                            ##STR15##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR16##      n-C.sub.3 H.sub.7                                                                             O   2                                           C.sub.10 H.sub.21                                                                              n-C.sub.3 H.sub.7                                                                             O   2                                           C.sub.9 H.sub.19                                                                               n-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.5 H.sub.11                                                                             n-C.sub.3 H.sub.7                                                                             O   2                                           sec-C.sub.4 H.sub.9                                                                            n-C.sub.3 H.sub.7                                                                             O   1                                           CH.sub.3        i-C.sub.3 H.sub.7                                                                             O   2   54-55                                   n-C.sub.3 H.sub.7                                                                              i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5359                i-C.sub.3 H.sub.7                                                                              i-C.sub.3 H.sub.7                                                                             O   2   44-45                                    ##STR17##      i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.3        i-C.sub.3 H.sub.7                                                                             S   2                                           CH.sub.3        i-C.sub.3 H.sub.7                                                                             O   1                                           n-C.sub.4 H.sub.9                                                                              i-C.sub.3 H.sub.7                                                                             O   2                                           i-C.sub.4 H.sub.9                                                                              i-C.sub.3 H.sub.7                                                                             O   2                                           sec-C.sub.4 H.sub.9                                                                            i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5316                sec-C.sub.4 H.sub.9                                                                            i-C.sub.3 H.sub.7                                                                             O   1                                           C.sub.2 H.sub.5 i-C.sub.3 H.sub.7                                                                             S   2                                           tert-C.sub.4 H.sub.9                                                                           i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.5 H.sub.11                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR18##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR19##      i-C.sub.3 H.sub.7                                                                             O   2                                           CH(C.sub.2 H.sub.5).sub.2                                                                      i-C.sub.3 H.sub.7                                                                             O   2                                           CH(C.sub.2 H.sub.5).sub.2                                                                      i-C.sub.3 H.sub.7                                                                             O   1                                           CH.sub.2 C(CH.sub.3).sub.3                                                                     i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2CH(CH.sub.3).sub.2                                                             i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5278                C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                              i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR20##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR21##      i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.6 H.sub.13                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR22##      i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.3 H.sub.7                                                                              i-C.sub.3 H.sub.7                                                                             O   1                                           n-C.sub.5 H.sub.11                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.7 H.sub.15                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.8 H.sub.17                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.9 H.sub.19                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                           n-C.sub.10 H.sub.21                                                                            i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR23##      i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5561                 ##STR24##      i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5610                CH.sub.3        n-C.sub.4 H.sub.9                                                                             O   2                                           C.sub.2 H.sub.5 n-C.sub.4 H.sub.9                                                                             O   2                                           n-C.sub.3 H.sub.7                                                                              n-C.sub.4 H.sub.9                                                                             O   2                                           n-C.sub.3 H.sub.7                                                                              n-C.sub.4 H.sub.9                                                                             S   2                                           i-C.sub.3 H.sub.7                                                                              n-C.sub.4 H.sub.9                                                                             O   2                                           n-C.sub.4 H.sub.9                                                                              n-C.sub.4 H.sub.9                                                                             O   2                                           i-C.sub.4 H.sub.9                                                                              n-C.sub.4 H.sub.9                                                                             O   2                                           tert-C.sub.4 H.sub.9                                                                           n-C.sub.4 H.sub.9                                                                             O   2                                            ##STR25##      n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.3        sec-C.sub.4 H.sub.9                                                                           O   2                                           C.sub.2 H.sub.5 sec-C.sub.4 H.sub.9                                                                           O   2   68-71                                   n-C.sub.3 H.sub.7                                                                              sec-C.sub.4 H.sub.9                                                                           O   2                                           i-C.sub.3 H.sub.7                                                                              sec-C.sub.4 H.sub.9                                                                           O   2                                           tert-C.sub.4 H.sub.9                                                                           sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.3        i-C.sub.4 H.sub.9                                                                             O   2                                           C.sub.2 H.sub.5 i-C.sub.4 H.sub.9                                                                             O   2                                           n-C.sub.3 H.sub.7                                                                              i-C.sub.4 H.sub.9                                                                             O   1                                           i-C.sub.3 H.sub.7                                                                              i-C.sub.4 H.sub.9                                                                             O   2                                           n-C.sub.4 H.sub. 9                                                                             i-C.sub.4 H.sub.9                                                                             S   2                                           CH.sub.3        tert-C.sub.4 H.sub.9                                                                          O   2                                           C.sub.2 H.sub.5 tert-C.sub.4 H.sub.9                                                                          O   2                                           n-C.sub.3 H.sub.7                                                                              tert-C.sub.4 H.sub.9                                                                          O   2                                           n-C.sub.4 H.sub.9                                                                              tert-C.sub.4 H.sub.9                                                                          O   1                                           CH.sub.3                                                                                        ##STR26##     O   2                                           C.sub.2 H.sub.5                                                                                 ##STR27##     O   2                                           tert-C.sub.4 H.sub.9                                                                            ##STR28##     O   2                                           CH.sub.3        CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                           C.sub.2 H.sub.5 CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                           n-C.sub.3 H.sub.7                                                                              CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                           i-C.sub.3 H.sub.7                                                                              CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                           tert-C.sub.4 H.sub.9                                                                           CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                            ##STR29##      i-C.sub.3 H.sub.7                                                                             O   2   111-115                                  ##STR30##      i-C.sub.3 H.sub.7                                                                             O   2   98-100                                  CH.sub.3                                                                                        ##STR31##     O   2                                           C.sub.2 H.sub.5                                                                                 ##STR32##     O   2                                           n-C.sub.3 H.sub.7                                                                               ##STR33##     O   2                                           tert-C.sub.4 H.sub.9                                                                            ##STR34##     O   2                                           CH.sub.3                                                                                        ##STR35##     O   2                                           C.sub.2 H.sub.5                                                                                 ##STR36##     O   2                                           n-C.sub.3 H.sub.7                                                                               ##STR37##     O   2                                           n-C.sub.3 H.sub.7                                                                               ##STR38##     O   2   68-73                                   n-C.sub.3 H.sub.7                                                                               ##STR39##     O   2                                           CH.sub.3        CH.sub.2CH.sub.2 Cl                                                                           O   2                                           n-C.sub.3 H.sub.7                                                                              CH.sub.2CH.sub.2 Cl                                                                           O   2                                           i-C.sub.3 H.sub.7                                                                              CH.sub.2CH.sub.2 Cl                                                                           O   2                                           i-C.sub.3 H.sub.7                                                                              CH.sub.2CH.sub.2 Cl                                                                           O   1                                           CH.sub.3                                                                                        ##STR40##     O   2                                           C.sub.2 H.sub.5                                                                                 ##STR41##     O   2                                           CH.sub. 3                                                                                       ##STR42##     O   2                                           n-C.sub.3 H.sub.7                                                                               ##STR43##     O   2                                           C.sub.2 H.sub.5                                                                                 ##STR44##     S   2                                           CHCH.sub.2      CH.sub.3       O   2                                           CCH             CH.sub.3       O   2                                           CHCHCH.sub.3    CH.sub.3       O   2                                           CCCH.sub.3      CH.sub.3       O   2                                           CH.sub.2CHCH.sub.2                                                                             CH.sub.3       O   2                                           CH.sub.2CCH     CH.sub.3       O   2   122-126                                 CH.sub.2CHCHCH.sub.3                                                                           CH.sub.3       O   2                                           CH.sub.2CCCH.sub.3                                                                             CH.sub.3       O   2                                            ##STR45##      CH.sub.3       O   2                                            ##STR46##      CH.sub.3       O   2                                            ##STR47##      CH.sub.3       O   2                                           CH.sub.2CH.sub.2CHCH.sub.2                                                                     CH.sub.3       O   2                                           CH.sub.2CH.sub.2CCH                                                                            CH.sub.3       O   2                                            ##STR48##      CH.sub.3       O   2                                            ##STR49##      CH.sub.3       O   2                                            ##STR50##      CH.sub.3       O   2                                            ##STR51##      CH.sub.3       O   2                                            ##STR52##      CH.sub.3       O   2                                            ##STR53##      CH.sub.3       S   2                                            ##STR54##      CH.sub.3       O   2                                           CH.sub.2C CH    CH.sub.3       O   1                                           CH.sub.2CCH     CH.sub.3       S   2                                           CHCH.sub.2      C.sub.2 H.sub.5                                                                               O   2                                           CCH             C.sub.2 H.sub.5                                                                               O   2                                           CHCHCH.sub.3    C.sub.2 H.sub.5                                                                               O   2                                           CCH.sub.3       C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CHCH.sub.2                                                                             C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CCH     C.sub.2 H.sub.5                                                                               O   2   71-75                                   CH.sub.2CHCHCH.sub.3                                                                           C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CCCH.sub.3                                                                             C.sub.2 H.sub.5                                                                               O   2                                            ##STR55##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR56##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR57##      C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CH.sub.2CHCH.sub.2                                                                     C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CH.sub.2CCH                                                                            C.sub.2 H.sub.5                                                                               O   2                                            ##STR58##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR59##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR60##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR61##      C.sub.2 H.sub.5                                                                               O   2                                            ##STR62##      C.sub.2 H.sub.5                                                                               O   2                                           CHCH.sub.2      n-C.sub.3 H.sub.7                                                                             O   2                                           CCH             n-C.sub.3 H.sub.7                                                                             O   2                                           CHCHCH.sub.3    n-C.sub.3 H.sub.7                                                                             O   2                                           CCHCH.sub.3     n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CHCH.sub.2                                                                             n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CCH     n-C.sub.3 H.sub.7                                                                             O   2   53-57                                   CH.sub.2CHCHCH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CCCH.sub.3                                                                             n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR63##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR64##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR65##      n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2CHCH.sub.2                                                                     n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2CCH                                                                            n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR66##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR67##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR68##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR69##      n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR70##      n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CCH     n-C.sub.3 H.sub.7                                                                             O   1                                           CH.sub.2CCH     n-C.sub.3 H.sub.7                                                                             S   2                                           CH CH.sub.2     i-C.sub.3 H.sub.7                                                                             O   2                                           CCH             i-C.sub.3 H.sub.7                                                                             O   2                                           CHCHCH.sub.3    i-C.sub.3 H.sub.7                                                                             O   2                                           CCCH.sub.3      i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH CH.sub.2                                                                            i-C.sub.3 H.sub.7                                                                             O   2   41-43                                   CH.sub.2CCH     i-C.sub.3 H.sub.7                                                                             O   2   108-112                                 CH.sub.2CHCHCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup.25 = 1.5436                 CH.sub.2CCCH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR71##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR72##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR73##      i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2CHCH.sub.2                                                                     i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2CCH                                                                            i-C.sub.3 H.sub.7                                                                             O   2   66-69                                    ##STR74##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR75##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR76##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR77##      i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR78##      i-C.sub.3 H.sub.7                                                                             O   2   114-115                                  ##STR79##      i-C.sub.3 H.sub.7                                                                             O   2   106-109                                  ##STR80##      i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CHCH.sub.2                                                                             i-C.sub.3 H.sub.7                                                                             S   2                                           CH.sub.2CCH     i-C.sub.3 H.sub.7                                                                             O   1                                            ##STR81##      i-C.sub.3 H.sub.7                                                                             O   2   71-73                                    ##STR82##      i-C.sub.3 H.sub.7                                                                             O   2   75-77                                   CH.sub.2CHCH.sub.2                                                                              ##STR83##     O   2                                           CH.sub.2CCH                                                                                     ##STR84##     O   2                                           CH.sub.2CCH                                                                                     ##STR85##     O   2                                           CH.sub.2CHCH.sub.2                                                                             n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CCH     n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CHCHCH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CCCH.sub.3                                                                             n-C.sub.4 H.sub.9                                                                             O   2                                            ##STR86##      n-C.sub.4 H.sub.9                                                                             O   2                                            ##STR87##      n-C.sub.4 H.sub.9                                                                             O   2                                           CHCH.sub.2      sec-C.sub.4 H.sub.9                                                                           O   2                                           CCH             sec-C.sub.4 H.sub.9                                                                           O   2                                           CHCHCH.sub.3    sec-C.sub.4 H.sub.9                                                                           O   2                                           CCCH.sub.3      sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CHCH.sub.2                                                                             sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CCH     sec-C.sub.4 H.sub.9                                                                           O   2   55-59                                   CH.sub.2CCH     sec-C.sub.4 H.sub.9                                                                           S   2                                           CH.sub.2CHCHCH.sub.3                                                                           sec-C.sub.4 H.sub.9                                                                           O   1                                           CH.sub.2CCCH.sub.3                                                                             sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR88##      sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR89##      sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR90##      sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2C  CH   CH(C.sub.2 H.sub.5).sub.2                                                                     O   2                                           CH.sub.2CCH                                                                                     ##STR91##     O   2                                           CH.sub.2CCH                                                                                     ##STR92##     O   2                                           CH.sub.2CCH                                                                                     ##STR93##     O   2                                           CH.sub.2CCH     CH.sub.2CH.sub.2 Cl                                                                           O   2                                           CH.sub.2CCH                                                                                     ##STR94##     O   2                                           CH.sub.2CCH                                                                                     ##STR95##     O   2                                           CH.sub.2CCH                                                                                     ##STR96##     O   2                                           CH.sub.2CCH                                                                                     ##STR97##     S   2                                           CH.sub.2CCH                                                                                     ##STR98##     O   2                                           CH.sub.2CH.sub.2 Cl                                                                            C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CH.sub.2 Br                                                                            i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup.25 = 1.5648                 CH.sub.2CH.sub.2 Cl                                                                            i-C.sub.3 H.sub.7                                                                             S   2                                           CH.sub.2CCCH.sub.2 Cl                                                                          i-C.sub.3 H.sub.7                                                                             O   2   68-72                                    ##STR99##      i-C.sub.3 H.sub.7                                                                             O   2   221                                      ##STR100##     i-C.sub.3 H.sub.7                                                                             O   2   170                                      ##STR101##     i-C.sub.3 H.sub.7                                                                             O   2   209-211                                  ##STR102##     i-C.sub.3 H.sub.7                                                                             O   2   89-90                                   CH.sub.2C CCH.sub.2 Cl                                                                         sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CHCHCH.sub.2 Cl                                                                        i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2 CH.sub.2OCH.sub.3                                                                     CH.sub.3       O   2                                           CH.sub.2CH.sub.2OCH.sub.3                                                                      C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CH.sub.2OCH.sub.3                                                                      n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2OCH.sub.3                                                                      i-C.sub.3 H.sub.7                                                                             O   2   62-63                                   CH.sub.2CH.sub.2OCH.sub.3                                                                      i-C.sub.3 H.sub.7                                                                             O   1                                           CH.sub.2CH.sub.2Oi-C.sub. 3 H.sub.7                                                            i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2OCH.sub.3                                                                      n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CH.sub.2OCH.sub.3                                                                      sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CH.sub.2SCH.sub.3                                                                      CH.sub.3       O   2                                           CH.sub.2CH.sub.2SCH.sub.3                                                                      n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2SCH.sub.3                                                                      i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2SCH.sub.3                                                                      n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CH.sub.2SCH.sub.3                                                                      sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub. 2CO.sub.2 CH.sub.3                                                                     CH.sub.3       O   2                                           CH.sub.2CO.sub.2 CH.sub.3                                                                      C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                     n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                     i-C.sub.3 H.sub.7                                                                             S   2                                           CH.sub.2 CO.sub.2 H                                                                            i-C.sub.3 H.sub.7                                                                             O   2   98                                      CH.sub.2CO.sub.2 CH.sub.3                                                                      n-C.sub.4 H.sub.9                                                                             O   2                                           CH.sub.2CO.sub.2 CH.sub.3                                                                      sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CO.sub.2 CH.sub.3                                                                      tert-C.sub.4 H.sub.9                                                                          O   2                                           CH.sub.2CH.sub.2 CO.sub.2 CH.sub.3                                                             i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR103##     i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CHCHCO.sub.2 CH.sub.3                                                                  i-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2 CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                             O   2   n.sub. D.sup.25 = 1.5459                 ##STR104##     i-C.sub.3 H.sub.7                                                                             O   2   n.sub. D.sup.25 = 1.5929                 ##STR105##     C.sub.2 H.sub.5                                                                               O   2                                            ##STR106##     n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR107##     i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup.25 = 1.5464                  ##STR108##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR109##     n-C.sub.2 H.sub.5                                                                             O   2                                            ##STR110##     i-C.sub.3 H.sub.7                                                                             O   2   82-86                                   CH.sub.2CCH                                                                                     ##STR111##    O   2                                            ##STR112##     i-C.sub.3 H.sub.7                                                                             O   2   69-73                                    ##STR113##                                                                                     ##STR114##    O   2                                           CH.sub.2C CH    CH.sub.2CCH    O   2                                           CH.sub.2CCH     CH.sub.2CCH    S   2                                            ##STR115##     CH.sub.3       O   2                                            ##STR116##     i-C.sub.3 H.sub.7                                                                             O   2   161-163                                  ##STR117##     C.sub.2 H.sub.5                                                                               O   2                                            ##STR118##     i-C.sub.3 H.sub.7                                                                             O   2   136-137                                  ##STR119##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR120##     i-C.sub.3 H.sub.7                                                                             O   2   132-133                                  ##STR121##     i-C.sub.3 H.sub.7                                                                             O   2   106                                      ##STR122##     n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2SCN     i-C.sub. 3 H.sub.7                                                                            O   2   124-126                                 CH.sub.2SCN     C.sub.2 H.sub.5                                                                               O   2                                           CH.sub.2CN      n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CN      i-C.sub.3 H.sub.7                                                                             O   2   119-121                                 CH.sub.2CN      i-C.sub.3 H.sub.7                                                                             S   2                                           CH.sub.2CN      i-C.sub.3 H.sub.7                                                                             O   1                                           CH.sub.2CH.sub.2 CN                                                                            n-C.sub.3 H.sub.7                                                                             O   2                                           CH.sub.2CH.sub.2 CN                                                                            i-C.sub.3 H.sub.7                                                                             O   2   115-117                                  ##STR123##     C.sub.2 H.sub.5                                                                               O   2                                            ##STR124##     n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR125##     i-C.sub.3 H.sub.7                                                                             O   2   139-141                                  ##STR126##     i-C.sub.3 H.sub.7                                                                             O   2   216-217                                  ##STR127##     n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR128##     C.sub.2 H.sub.5                                                                               O   2                                            ##STR129##     i-C.sub.3 H.sub.7                                                                             O   2   105-107                                  ##STR130##                                                                                     ##STR131##    O   2                                            ##STR132##     i-C.sub.3 H.sub.7                                                                             O   2   101-102                                 CH.sub.2NHCO.sub.2 C.sub.2 H.sub.5                                                             i-C.sub.3 H.sub.7                                                                             O   2   186                                      ##STR133##     i-C.sub.3 H.sub.7                                                                             O   2   153-156                                  ##STR134##     i-C.sub.3 H.sub.7                                                                             O   2   138-140                                  ##STR135##     i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR136##     i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR137##     n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR138##     i-C.sub.3 H.sub.7                                                                             O   2   141-143                                  ##STR139##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR140##     i-C.sub.3 H.sub.7                                                                             O   2   139-141                                  ##STR141##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR142##     i-C.sub.3 H.sub.7                                                                             O   2                                            ##STR143##     n-C.sub.3 H.sub.7                                                                             O   2                                            ##STR144##     i-C.sub.3 H.sub.7                                                                             O   2   85-87                                    ##STR145##     sec-C.sub.4 H.sub. 9                                                                          O   2                                            ##STR146##     C.sub.2 H.sub.5                                                                               O   0                                            ##STR147##     i-C.sub.3 H.sub.7                                                                             O   2   139-141                                  ##STR148##     i-C.sub.3 H.sub.7                                                                             O   2   124-126                                  ##STR149##     i-C.sub.3 H.sub.7                                                                             O   2   70                                       ##STR150##     i-C.sub.3 H.sub.7                                                                             O   2   79-80                                    ##STR151##     C.sub.2 H.sub.5                                                                               O   2                                            ##STR152##     i-C.sub.3 H.sub.7                                                                             O   2   107                                      ##STR153##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR154##     i-C.sub.3 H.sub.7                                                                             O   2   110-113                                  ##STR155##     i-C.sub.3 H.sub.7                                                                             O   2   73-76                                    ##STR156##     sec-C.sub.4 H.sub.9                                                                           O   2                                            ##STR157##     i-C.sub.3 H.sub.7                                                                             O   2   72-74                                    ##STR158##     i-C.sub.3 H.sub.7                                                                             O   2   101-102                                  ##STR159##     i-C.sub.3 H.sub.7                                                                             O   2   91-92                                    ##STR160##     i-C.sub.3 H.sub.7                                                                             O   2   181                                     CH.sub.2NP(OC.sub.2 H.sub.5).sub.3                                                             i-C.sub.3 H.sub.7                                                                             O   2   n.sub.D.sup. 25 = 1.5072                CH.sub.2CH.sub.2 OH                                                                            sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2CH.sub.2 OH                                                                             ##STR161##    O   2                                           CH.sub.2CH.sub.2 OH                                                                             ##STR162##    O   2                                           CH.sub.2CH.sub.2 OH                                                                            C.sub.6 H.sub.5                                                                               O   2                                           CH.sub.2CH.sub.2 OH                                                                             ##STR163##    O   2                                           CH.sub.2CH.sub.2 OH                                                                             ##STR164##    O   2                                           CH.sub.2CH.sub.2 OH                                                                             ##STR165##    O   2                                           CH.sub.2 SCN    sec-C.sub.4 H.sub.9                                                                           O   1                                           CH.sub.2 CN     sec-C.sub.4 H.sub.9                                                                           O   2                                           CH.sub.2 SCN                                                                                    ##STR166##    O   2                                           CH.sub.2 SCN                                                                                    ##STR167##    O   2                                           CH.sub.2 SCN                                                                                    ##STR168##    O   2                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                     C.sub.6 H.sub.5                                                                               O   2                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                      ##STR169##    O   2                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                      ##STR170##    S   2                                           (CH.sub.2).sub.4 OH                                                                            i-C.sub.3 H.sub.7                                                                             O   2                                           __________________________________________________________________________     X      Ring position                                                                         m R.sup.1        R.sup.2 Y n m.p. (°C.)                   __________________________________________________________________________     CH.sub.3                                                                              5,6,7  1 CH.sub.3       i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              8      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 140-144                             CH.sub.3                                                                              8      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      S 2                                     CH.sub.3                                                                              8      1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              7      1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6    1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2CCCH.sub.2 Cl                                                                         i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 tert-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 tert-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                                      S 2                                     CH.sub.3                                                                              6,8    2 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 98-101                              CH.sub.3                                                                              6,8    2 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              6,8    2 CH.sub.2SCN    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR171##    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR172##    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2CO.sub.2 CH.sub.3                                                                     i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR173##    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR174##    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR175##    i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1                                                                                 ##STR176##    sec-C.sub.4 H.sub.9                                                                    O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2CH.sub.2 CN                                                                           i-C.sub.3 H.sub.7                                                                      O 1                                     CH.sub.3                                                                              8      1 CH.sub.2CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                      O 2 83-86                               Cl     7      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 97-103                              Cl     7      1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     5,6,7,8                                                                               1 tert-C.sub.4 H.sub.9                                                                          sec-C.sub.4 H.sub.9                                                                    O 2                                     CH.sub.3                                                                              5      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 87-91                               Cl     5,6,7,8                                                                               1 CH.sub.2CCCH.sub.2 Cl                                                                          ##STR177##                                                                            O 2                                     I      6      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 105-109                             Cl     8      1 CH.sub.2 SCN   i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     5,6,7  1 CH.sub.2 SCN   i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     5,6,7,8                                                                               1 CH.sub.2 CO.sub.2 CH.sub.3                                                                    sec-C.sub.4 H.sub.9                                                                    O 2                                     Cl     5,6,7,8                                                                               1                                                                                 ##STR178##                                                                                    ##STR179##                                                                            O 2                                     Cl     7      1 CH.sub.2CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                      O 2 93-96                               Cl     5,6,8  1 CH.sub.2CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     7      1                                                                                 ##STR180##    i-C.sub.3 H.sub.7                                                                      O 2 94-97                               F      5,6,7,8                                                                               1                                                                                 ##STR181##    i-C.sub.3 H.sub.7                                                                      O 2                                     F      5,6,7,8                                                                               1                                                                                 ##STR182##    sec-C.sub.4 H.sub.9                                                                    S 2                                     F      5,6,7,8                                                                               1                                                                                 ##STR183##    i-C.sub.3 H.sub.7                                                                      O 2                                     F      5,6,7,8                                                                               1                                                                                 ##STR184##    i-C.sub.3 H.sub.7                                                                      O 2                                     C.sub.6 H.sub.5                                                                       8      1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     C.sub.6 H.sub.5                                                                       5,6,7,8                                                                               1 CH.sub.2 SCN   sec-C.sub.4 H.sub.9                                                                    O 2                                     C.sub.6 H.sub.5                                                                       5,6,7,8                                                                               1 CH.sub.2 CH.sub.2 OH                                                                           ##STR185##                                                                            O 2                                     Br     6      1 CH.sub.3       i-C.sub.3 H.sub.7                                                                      O 1 135-137                             Br     6      1 CH.sub.2 C.sub.6 H.sub.5                                                                      i-C.sub.3 H.sub.7                                                                      O 1 110-111                             C.sub.6 H.sub.5                                                                       5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                               ##STR186##                                                                            O 2                                     Cl     8      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2 86-90                               SCN    5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     SCN    5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     SCN    5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      S 2                                     SCN    5,6,7,8                                                                               1 CH.sub.2 CO.sub.2 CH.sub.3                                                                    i-C.sub.3 H.sub.7                                                                      S 2                                     SCN    5,6,7,8                                                                               1 CH.sub.2 SCN   sec-C.sub.4 H.sub.9                                                                    O 1                                     SCN    5,6,7,8                                                                               1                                                                                 ##STR187##    i-C.sub.3 H.sub.7                                                                      O 2                                     CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1 CH.sub.2 SCN   i-C.sub.3 H.sub.7                                                                      O 2                                     CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2                                     CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1 CH.sub.2CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                      O 2                                     N(CH.sub.3).sub.2                                                                     5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     N(CH.sub.3).sub.2                                                                     5,6,7,8                                                                               1                                                                                 ##STR188##    i-C.sub.3 H.sub.7                                                                      O 2                                     N(CH.sub.3).sub.2                                                                     5,6,7,8                                                                               1 tert-C.sub.4 H.sub.9                                                                          sec-C.sub.4 H.sub.9                                                                    O 2                                     OCH.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2C CH   i-C.sub.3 H.sub.7                                                                      O 2                                     OCH.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2 SCN   i-C.sub.3 H.sub.7                                                                      O 2                                     SCH.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     SCH.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2CCH                                                                                    ##STR189##                                                                            O 1                                     SCH.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2CCCH.sub.2 Cl                                                                         i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     6      1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 1 92-94                               Cl     6      1 CH.sub.2 C.sub.6 H.sub.5                                                                      C.sub.2 H.sub.5                                                                        O 1 105-109                             SO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     SO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                               1                                                                                 ##STR190##    i-C.sub.3 H.sub.7                                                                      O 2                                     SO.sub.2 N(CH.sub.3).sub.2                                                            5,6,7,8                                                                               1                                                                                 ##STR191##    i-C.sub.3 H.sub.7                                                                      O 2                                     SO.sub.2 N(CH.sub.3).sub.2                                                            5,6,7,8                                                                               1 CH.sub.2CH.sub.2 OH                                                                           i-C.sub.3 H.sub.7                                                                      O 2                                     CCl.sub.3                                                                             5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     SO.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                               1 CH.sub.2 CN    sec-C.sub.4 H.sub.9                                                                    O 2                                     CCl.sub.3                                                                             5,6,7,8                                                                               1                                                                                 ##STR192##    i-C.sub.3 H.sub.7                                                                      O 2                                     CF.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     CF.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2                                     CF.sub.3                                                                              5,6,7,8                                                                               1 CH.sub.2 CO.sub.2 CH.sub.3                                                                    sec-C.sub.4 H.sub.9                                                                    S 2                                      ##STR193##                                                                           5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                      ##STR194##                                                                           5,6,7,8                                                                               1 CH.sub.2 SCN   i-C.sub.3 H.sub.7                                                                      O 2                                      ##STR195##                                                                           5,6,7,8                                                                               1 CH.sub.2 CH.sub.2 CN                                                                          i-C.sub.3 H.sub.7                                                                      O 2                                     OH     5,6,7,8                                                                               1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2                                     SH     5,6,7,8                                                                               1 CH.sub.2CCH    i-C.sub.3 H.sub.7                                                                      O 2                                     SO.sub.2 NHCH.sub.3                                                                   5,6,7,8                                                                               1                                                                                 ##STR196##    i-C.sub.3 H.sub.7                                                                      O 2                                     OCF.sub.2 CH.sub.3                                                                    5,6,7,8                                                                               1 CH.sub.2CCCH.sub.2 Cl                                                                         i-C.sub.3 H.sub.7                                                                      O 1                                     OCF.sub.2 CF.sub.3                                                                    5,6,7,8                                                                               1 tert-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                                      O 2                                     OCF.sub.2 CF.sub.3                                                                    5,6,7,8                                                                               1                                                                                 ##STR197##    i-C.sub.3 H.sub.7                                                                      O 2                                     OCF.sub.2 CCl.sub.3                                                                   5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     Cl     6      1 CH.sub.3       C.sub.2 H.sub.5                                                                        O 1 96-98                               Br     6      1 CH.sub.3       C.sub.2 H.sub.5                                                                        O 1 104-105                             NO.sub.2                                                                              6      1 CH.sub.2 SCN                                                                                   ##STR198##                                                                            O 2                                     NO.sub.2                                                                              6      1 CH.sub.2 N.sub.3                                                                              CH.sub.2CHCH.sub.2                                                                     O 2                                     NO.sub.2                                                                              8      1 CH.sub.2 CN                                                                                    ##STR199##                                                                            O 2                                     NO.sub.2                                                                              5,7    1 CH.sub.2 CO.sub.2 CH.sub.3                                                                    i-C.sub.3 H.sub.7                                                                      O 2                                     NO.sub.2                                                                              6                                                                                     2 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 2                                     CH.sub.3                                                                              8                                                                       NO.sub.2                                                                              5,6,7,8                                                                               1                                                                                 ##STR200##    i-C.sub.3 H.sub.7                                                                      O 2                                     NO.sub.2                                                                              5,6,7,8                                                                               1 CH.sub.2 SCN   C.sub.6 H.sub.5                                                                        O 2                                     NO.sub.2                                                                              6      1 CH.sub.2 SCN                                                                                   ##STR201##                                                                            O 2                                     CH.sub.2 F                                                                            5,6,7,8                                                                               1 CH.sub.2 N.sub.3                                                                              i-C.sub.3 H.sub.7                                                                      O 1                                     CH.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                               1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                      ##STR202##                                                                           8      1 CH.sub.2 CN    i-C.sub.3 H.sub.7                                                                      O 2                                     --     --     0 CH.sub.2 N.sub.3                                                                              CH.sub.3                                                                               O 2 108                                 --     --     0                                                                                 ##STR203##    i-C.sub.3 H.sub.7                                                                      O 2 137                                 --     --     0                                                                                 ##STR204##    i-C.sub.3 H.sub.7                                                                      O 2 68                                  --     --     0 CH.sub.2NP(OCH.sub.3).sub.3                                                                   i-C.sub.3 H.sub.7                                                                      O 2 viscous oil                         --     --     0                                                                                 ##STR205##    i-C.sub.3 H.sub.7                                                                      O 2 n.sub.D.sup.20 = 1.5497             --     --     0                                                                                 ##STR206##    i-C.sub.3 H.sub.7                                                                      O 2 129-132                             --     --     0                                                                                 ##STR207##    i-C.sub.3 H.sub.7                                                                      O 2 146-148                             __________________________________________________________________________

EXAMPLE 6 Herbicidal action of the new 2,1,3-benzothiadiazine compounds

Greenhouse experiments and experiments in the open were carried out in order to study the herbicidal and selective properties of the new compounds.

I. Greenhouse experiments

Plastic flowerpots having a volume of 300 cm³ were filled with a sandy loam, and test plants were grown therein, separated by species.

The plants were either grown from seed, or from pregerminated tubers (e.g., Cyperus esculentus) or from transplanted vegetatively reproduced species. For the preemergence treatment, only seeds were suitable. The active ingredients were suspended or emulsified in water as distributing agent, and sprayed onto the surface of the soil by means of atomizing nozzles. After treatment, the vessels were lightly sprinkler-irrigated, and then covered with transparent plastic hoods until the plants emerged. In postemergence treatment (leaf treatment) the plants were first grown to a height of from 3 to 10 cm, depending on their habit, before being treated. The plants were of course not sprinkler-irrigated immediately, and no hoods were placed on the pots. The test plants were placed in either the cooler or warmer sections of the greenhouse, depending on their temperature requirements. The experimental period was from 2 to 4 weeks. During this period the plants were tended and their reactions to the various treatments were evaluated. The application rates of the compounds under investigation are given as kg of active ingredient per hectare. Assessment was on a 0 to 100 scale, 0 denoting no damage or normal emergence, and 100 denoting no emergence or destruction of the plants.

II. Experiments in the open

Here, postemergence treatments were carried out on small plots. The active ingredients were applied as an emulsion or suspension in water as carrier and distribution medium, with the aid of a motor-driven plot spray mounted on a hitch. All the experiments were observed for several weeks and also assessed on the 0 to 100 scale.

Results

The representatives of the new compounds listed in Tables 2 to 6 control unwanted plants better than the comparative agent 1-chloromethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, and have an action similar to, and sometimes poorer than, that of comparative agent 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide. Tolerance was in some crops the same as that of the comparative agents. However, in crops in which prior art agents from this class of compounds cannot be used, or only at considerable risk, such as potatoes, onions and sunflowers (these only being given by way of example), the compounds according to the invention proved to be far better tolerated; this is their value and the advance they represent.

                  TABLE 1                                                          ______________________________________                                         List of plant names                                                                          Abbreviation                                                     Botanical name                                                                               in tables    English term                                        ______________________________________                                         Abutilon theophrastii                                                                        Abut. theo.  velvet leaf                                         Allium cepa     --         onion                                               Amaranthus spp.                                                                              Amar. spp.   pigweed                                             Ammania coccinea                                                                             Amman. cocc. redstem                                             Chenopodium spp.                                                                             Chenop. spp. lambsquarters                                       Chrysanthemum segetum                                                                        Chrys. seget.                                                                               corn marigold                                       Cucumis sativus                                                                              Cucumis sat. cucumber                                            Cyperus esculentus                                                                           Cyper. escul.                                                                               yellow nutsedge                                     Datura stramonium                                                                            Datura stram.                                                                               Jimsonweed                                          Galium aparine                                                                               Gali. apar.  catchweed bedstraw                                  Galinsoga spp.                                                                               Galins. app. gallant soldier                                     Glycine max     --         soybean                                             Helianthus annuus                                                                            Helianth. annuus                                                                            sunflower                                           Hordium vulgare                                                                              Hord. vulg.  barley                                              Laminum spp.    --         deadnettle                                          Matricaria spp.                                                                              Matric. spp. chamomile                                           Medicago sativa                                                                              Medic. sat.  alfalfa                                             Mentha piperita                                                                              Mentha pip.  peppermint                                          Oryza sativa  Oryza sat.   rice                                                Phaseolus vulgaris                                                                           Phaseol. vulg.                                                                              snapbean                                            Raphanus spp.   --         wild radish                                         Sida spinosa  Sida spin.   prickly sida                                        Sinapis spp.    --         yellow charlock                                     Solanum nigrum                                                                               Solan. nigr. black nightshade                                    Solanum tuberosum                                                                            Solan. tub.  potato                                              Stellaria media                                                                              Stell. med.  chickweed                                           Zea mays        --         Indian corn                                         ______________________________________                                    

                                      TABLE 2                                      __________________________________________________________________________     Selective herbicidal action in vegetables; postemergence treatment in the      greenhouse                                                                      ##STR208##                                                                                   Application                                                                          Test plants and % damage                                  Compound                                                                             Substituent                                                                             rate  Allium                                                                             Cucumis                                                                             Phaseol.                                                                            Abut.                                                                             Datura                                                                             Lamium                                                                              Solan.                                                                             Stell.                      no.   R        kg/ha cepa                                                                               sat. vulg.                                                                               theo.                                                                             stram.                                                                             spp. nigr.                                                                              med.                        __________________________________________________________________________                    0.5   10  0    0    78  95 80   57  83                          1     CH.sub.2CCH                                                                             1.0   20  0    0    82 --  80   80  97                                         2.0   25  0    0    88 --  100  93  97                                         0.5    0  0    0    98 100 80   82  70                          2     CH.sub.2CN                                                                              1.0   10  0    0    98 --  100  82  100                                        2.0   20  10   0    98 --  --   98  100                                        0.5   30  0    0    48  95 60   20  58                          3     CH.sub.2Cl                                                                              1.0   32  0    0    52 --  60   20  80                                (prior art)                                                                             2.0   40  0    0    52 --  100  40  95                                         0.5   63  0    0    68 100 50   88  82                          4     H        1.0   65  5    0    72 --  50   92  88                                (prior art)                                                                             2.0   65  10   0    78 --  100  98  95                          __________________________________________________________________________      0 = no damage                                                                  100 = plants destroyed                                                   

                                      TABLE 3                                      __________________________________________________________________________     Selective herbicidal action in sunflowers and other crops; postemergence       treatment                                                                      in the greenhouse                                                               ##STR209##                                                                                     Application                                                                          Test plants and % damage                                Compound                                                                             Substituent                                                                               rate  Helianth.                                                                           Hord.                                                                              Zea                                                                               Datura                                                                             Sida                                                                              Stell.                               no.     R        kg/ha annuus                                                                              vulg.                                                                              mays                                                                              stram.                                                                             spin.                                                                             med.                                 __________________________________________________________________________            ##STR210##                                                                               2.0 4.0                                                                              0 5  0 0 5 10                                                                              95 --                                                                              95 --                                                                             65 --                                4     H          2.0   100  0   0  100 93 95                                                    4.0   100  0   7  --  -- --                                   6     CH.sub.2CHCH.sub.2                                                                        2.0   0    0   0  95  -- 50                                                    4.0   10   0   0  --  -- --                                   7     CH.sub.2CH.sub.2CH.sub.3                                                                  2.0   0    0   0  95  -- 80                                                    4.0   0    0   12 --  -- --                                   __________________________________________________________________________      0 = no damage                                                                  100 = plants destroyed                                                   

                                      TABLE 4                                      __________________________________________________________________________     Action and selectivity; postemergence treatment in the greenhouse               ##STR211##                                                                                Appli-                                                                             Test plants and % damage                                       Com-        cation      Men-                                                                              Ory-                                                pound                                                                              Substituent                                                                            rate                                                                               Hord.                                                                              Medic.                                                                             tha.                                                                              za Zea                                                                               Amar.                                                                              Amman.                                                                              Cyper.                                                                             Chenop.                                                                             Chrys.                                                                             Galium                                                                             Matri.              no. R       kg/ha                                                                              vulg.                                                                              sat.                                                                               pip.                                                                              sat.                                                                              mays                                                                              spp.                                                                               cocc.                                                                               escul.                                                                             spp. seget.                                                                             apar.                                                                              spp.                __________________________________________________________________________                 0.5 0   --  0  0  0  100 10   33  100  100 33  100                 8   CH.sub.2N.sub.3                                                                        1.0 0   0   0  0  0  100 70   32  100  100 82  100                             4.0 0   0   0  8  0  --  --   42  --   --  95  100                             0.5 0   --  -- 0  0  15  95   50  --   100 --  100                 9   CH.sub.2SCN                                                                            1.0 0   --  -- 0  10 20  95   60  --   100 --  100                             4.0 0   --  -- 20 10 --  --   95  --   --  --  --                              0.5 --  --  0  0  5  75  --   10  --    92 10  100                 3   CH.sub.2 Cl                                                                            1.0 --  0   0  0  5  75  --   15  --    98 60  100                             4.0 --  20  0  0  10 --  --   35  --   --  --  --                              0.5 0   --  0  0  0  23  85   26  100   99 50  100                 4   H       1.0 0   0   0  0  0  43  88   34  100   99 60  100                             4.0 0   20  0  0  7  --  --   60  --   --  --  --                  __________________________________________________________________________                                                                2                    100 = plants destroyed                                                         0 = no action                                                            

                                      TABLE 5                                      __________________________________________________________________________     Selective herbicidal action; postemergence treatment in the open               Application Test plants and % damage                                           Compound                                                                             rate  Glyc.                                                                              Solan.                                                                             Zea                                                                               Chenop.                                                                             Galins.                                                                            Gali.                                                                             Sinapis/                                    no.   kg/ha max.                                                                               tub.                                                                               mays                                                                              spp. spp.                                                                               apar.                                                                             Raphanus                                    __________________________________________________________________________     8     2.0   5    4  0  94   95   88                                                                               100                                         9     1.0   2   --  0  86   92  -- 100                                               2.0   5   --  -- --   --  -- --                                          2     1.0   10  --  0  53   13  100                                                                                90                                               2.0   --  --  -- 75   20  100                                                                                90                                         4     2.0   6   14  0  90   95   88                                                                               100                                         __________________________________________________________________________      0 = no damage                                                                  100 = plants destroyed                                                   

                  TABLE 6                                                          ______________________________________                                         Pre- and postemergence treatment with                                          new 2,1,3-benzothiadiazine derivatives                                         in the greenhouse                                                               ##STR212##                                                                    Com-                              Test plant and                               pound                             % damage                                     no.   Substituent  kg/ha   Method Sida spinosa                                 ______________________________________                                         10                                                                                    ##STR213##  1.0 2.0 1.0 2.0                                                                        pre pre post  post                                                                    95  95 95 95                                                    1.0     pre    60                                                              2.0     pre    60                                           4     H                                                                                           1.0     post   95                                                              2.0     post   95                                                              1.0     pre    80                                                              2.0     pre    92                                           8     CH.sub.2N.sub.3                                                                             1.0     post   78                                                              2.0     post   95                                           ______________________________________                                          0 = no damage                                                                  100 = plants destroyed                                                         pre = preemergence treatment                                                   post = postemergence treatment                                           

                                      TABLE 7                                      __________________________________________________________________________     Biological action of new 2,1,3-benzothiadiazine derivatives on Sinapis         alba;                                                                          postemergence treatment in the greenhouse                                       ##STR214##                                                                    Compound                                                                             Substituents         Ring     Sinapis alba and                           no.   R.sup.1      R.sup.2                                                                              X position                                                                            kg/ha                                                                              % damage                                   __________________________________________________________________________      ##STR215##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2CCH        C.sub.4 H.sub.9 sec                                                                  H --   2.0 100                                        CH.sub.2CH.sub.2 Br                                                                               C.sub.3 H.sub.7 i                                                                    H --   2.0 75                                         CH.sub.2CCCH.sub.2 Cl                                                                             C.sub.3 H.sub.7 i                                                                    H --   2.0 90                                          ##STR216##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2 COCH.sub.3                                                                               C.sub.3 H.sub.7 i                                                                    H --   2.0 90                                          ##STR217##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2 CH.sub.2 CN                                                                              C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR218##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR219##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR220##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR221##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR222##        C.sub.3 H.sub.7 i                                                                    H --   2.0 80                                          ##STR223##        C.sub. 3 H.sub.7 i                                                                   H --   2.0 100                                         ##STR224##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR225##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2 NP(OC.sub.2 H.sub.5).sub.3                                                               C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2 CCH       C.sub.3 H.sub.7 i                                                                    Cl                                                                               7    2.0 100                                        CH.sub.2 CCH       C.sub.3 H.sub.7 i                                                                    Cl                                                                               8    2.0 80                                         CH.sub.2N.sub.3    CH.sub.3                                                                             H --   2.0 100                                         ##STR226##        C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                        CH.sub.2NP(OCH.sub.3).sub.3                                                                       C.sub.3 H.sub.7 i                                                                    H --   2.0 100                                         ##STR227##        C.sub. 3 H.sub.7 i                                                                   H --   2.0 100                                        __________________________________________________________________________      0 = no damage                                                                  100 = plants destroyed                                                   

The new active ingredients may be used for controlling unwanted plant growth in the following crops:

    ______________________________________                                         Botanical name      English term                                               ______________________________________                                         Ananas comosus      pineapple                                                  Arachis hypogaea    peanuts (groundnuts)                                       Asparagus officinalis                                                                              asparagus                                                  Avena sativa        oats                                                       Beta vulgaris spp. altissima                                                                       sugarbeet                                                  Beta vulgaris spp. rapa                                                                            fodder beet                                                Beta vulgaris spp. esculenta                                                                       table beet, red beet                                       Brassica napus var. napus                                                                          rape                                                       Brassica napus var. napobrassica                                               Brassica napus var. rapa                                                                           turnips                                                    Brassica rapus var. silvestris                                                 Camellia sinensis   tea plants                                                 Carthamus tinctorius                                                                               safflower                                                  Citrus limon        lemon                                                      Citrus maxima       grapefruit                                                 Citrus reticulata                                                              Citrus sinensis     orange trees                                               Caffea arabica (Coffea canephora,                                                                  coffee plants                                              Coffea liberica)                                                               Cucumis melo        melons                                                     Cynodon dactylon    Bermudagrass in turf and                                                       lawns                                                      Daucus carota       carrots                                                    Elaeis guineensis   oil palms                                                  Fragaria vesca      strawberries                                               Gossypium hirsutum                                                             (Gossypium arboreum                                                            Gossypium herbaceum cotton                                                     Gossypium vitifolium)                                                          Helianthus tuberosus                                                           Hevea brasiliensis  rubber plants                                              Humulus lupulus     hops                                                       Iopmoea batatas     sweet potatoes                                             Lactuca sativa      lettuce                                                    Lens culinaris      lentils                                                    Linum usitatissimum flax                                                       Lycopersicon lycopersicum                                                                          tomatoes                                                   Malus spp.          apple trees                                                Manihot esculenta   cassava                                                    Musaspp.            banana plants                                              Nicotiana tabacum                                                              (N. rustica)        tobacco                                                    Olea europaea       olive trees                                                Panicum miliaceum                                                              Phaseolus lunatus   limabeans                                                  Phaseolus mungo     mungbeans                                                  Pennisetum glaucum                                                             Petroselinum crispum                                                                               parsley                                                    spp. tuberosum                                                                 Picea abies         Norway spruce                                              Abies alba          fir trees                                                  Pinus spp.          pine trees                                                 Pisum sativum       English peas                                               Prunus avium        cherry trees                                               Prunus domestica    plum trees                                                 Prunus persica      peach trees                                                Pyrus communis      pear trees                                                 Ribes sylvestre     redcurrants                                                Ribes uva-crispa                                                               Ricinus communis                                                               Saccharum officinarum                                                                              sugar cane                                                 Secale cereale rye                                                             Sesamum indicum     Sesame                                                     Sorghum bicolor (s. vulgare)                                                                       grain sorghum                                              Sorghum dochna                                                                 Spinacia oleracea   spinach                                                    Theobroma cacao     cacao plants                                               Trifolium pratense  red clover                                                 Triticum aestivum   wheat                                                      Vaccinium corymbosum                                                                               blueberries                                                Vaccinium vitis-idaea                                                                              cranberries                                                Vicia faba          tick beans                                                 Vigna sinensis (V. unguiculata)                                                                    cow peas                                                   Vitis vinifera      grapes                                                     ______________________________________                                    

To further increase the spectrum of action of the new individual active ingredients, to achieve synergistic effects or to improve persistence in the soil, numerous other herbicidal compounds and growth regulators may be used as components for mixtures and combination. Depending on the area of use and the unwanted plants to be controlled, the following substances or similar derivatives are suitable as components: ##STR228## and salts

    ______________________________________                                          ##STR229##                                                                    R               R.sup.1       R.sup.2                                          ______________________________________                                          ##STR230##     NH.sub.2      Cl                                                ##STR231##     NHCH.sub.3    Cl                                               ______________________________________                                    

    ______________________________________                                          ##STR232##                                                                    R      R.sup.1   R.sup.2  R.sup.3  R.sup.4                                     ______________________________________                                         H      SO.sub.2 NH.sub.2                                                                        H        n . C.sub.3 H.sub.7                                                                     n . C.sub.3 H.sub.7                         H.sub.3 C                                                                             H.sub.3 C H        H                                                                                        ##STR233##                                 ______________________________________                                    

    ______________________________________                                          ##STR234##                                                                    R              R.sup.1  R.sup.2                                                ______________________________________                                          ##STR235##    H                                                                                        ##STR236##                                            ______________________________________                                    

    ______________________________________                                          ##STR237##                                                                                R.sup.1                                                                               R.sup.2                                                     ______________________________________                                          ##STR238##   H        CH.sub.2CCCH.sub.2 Cl                                    ##STR239##   H        i-C.sub. 3 H.sub.7                                       ##STR240##   H        CH.sub.3                                                ______________________________________                                    

    ______________________________________                                          ##STR241##                                                                    R         R.sup.1                R.sup.2                                       ______________________________________                                          ##STR242##                                                                              H                      CH.sub.3                                       ##STR243##                                                                              H                      C.sub.2 H.sub.5                                ##STR244##                                                                              CH.sub.3               CH.sub.3                                       ##STR245##                                                                              H                      CH.sub.3                                                 ##STR246##                                                                     ##STR247##                                                          ______________________________________                                    

    ______________________________________                                          ##STR248##                                                                    R                  X       Y        R.sup.1                                    ______________________________________                                         CH.sub.3           Cl      Cl       Na                                          ##STR249##        Cl      H        CH.sub.3                                    ##STR250##        H       H        H salts                                     ##STR251##        H       CH.sub.3 CH.sub.3                                    ##STR252##        H       CH.sub.3 C.sub.2 H.sub.5                             ##STR253##        H       CH.sub.3 i . C.sub.3 H.sub.7                         ##STR254##        H       CH.sub.3 CH.sub.3                                   ______________________________________                                    

    ______________________________________                                          ##STR255##                                                                    R                X      Y       R.sup.1                                        ______________________________________                                          ##STR256##      H      CH.sub.3                                                                                ##STR257##                                     ##STR258##      H      CH.sub.3                                                                               Na                                              ##STR259##      H      CH.sub.3                                                                               Na                                             ______________________________________                                    

    ______________________________________                                          ##STR260##                                                                    R    R.sup.1    X        R.sup.2                                                                               R.sup.3                                        ______________________________________                                         H    tert . C.sub.4 H.sub.9                                                                    SCH.sub.3                                                                               H      C.sub.2 H.sub.5                                H    i . C.sub.3 H.sub.7                                                                       SCH.sub.3                                                                               H      i . C.sub.3 H.sub.7                            H    C.sub.2 H.sub.5                                                                           SCH.sub.3                                                                               H      C.sub.2 H.sub.5                                H    i . C.sub.3 H.sub.7                                                                       SCH.sub.3                                                                               H      C.sub.2 H.sub.5                                H    i . C.sub.3 H.sub.7                                                                       Cl       H      C.sub.2 H.sub.5                                H    i . C.sub.3 H.sub.7                                                                       Cl       H                                                                                      ##STR261##                                    H    C.sub.2 H.sub.5                                                                           Cl       H      C.sub.2 H.sub.5                                H    C.sub.2 H.sub.5                                                                           Cl       H                                                                                      ##STR262##                                    H    i . C.sub.3 H.sub.7                                                                       Cl       H      i . C.sub.3 H.sub.7                            H    i . C.sub. 3 H.sub.7                                                                      OCH.sub.3                                                                               H      i . C.sub.3 H.sub.7                            H    C.sub.2 H.sub.5                                                                           Cl       H                                                                                      ##STR263##                                    H    C.sub.2 H.sub.5                                                                           Cl       H                                                                                      ##STR264##                                          ##STR265##                                                                               Cl       H                                                                                      ##STR266##                                    ______________________________________                                    

    ______________________________________                                          ##STR267##                                                                    R                R.sup.1 R.sup.2                                               ______________________________________                                          ##STR268##      H                                                                                       ##STR269##                                            ##STR270##      H       C.sub.2 H.sub.5                                        ##STR271##      H                                                                                       ##STR272##                                            ##STR273##      H                                                                                       ##STR274##                                            ##STR275##      H       CH.sub.3                                              ______________________________________                                    

    ______________________________________                                          ##STR276##                                                                    X    Y                        R                                                ______________________________________                                         Br   Br                       H salts                                          I    I                        H salts                                                ##STR277##              salts, esters                                          ##STR278##              salt, esters                                     ______________________________________                                    

    ______________________________________                                          ##STR279##                                                                      R               R.sup.1                                                                               R.sup.2                                                                               R.sup.3                                        ______________________________________                                          ##STR280##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR281##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR282##       CH.sub.3                                                                              CH.sub.3                                                                              H                                              ______________________________________                                          ##STR283##                                                                      R               R.sup.1                                                                               R.sup.2                                                                               R.sup.3                                        ______________________________________                                          ##STR284##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR285##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR286##       H      CH.sub.3                                                                               ##STR287##                                     ##STR288##       H      CH.sub.3                                                                              OCH.sub.3                                       ##STR289##       H      CH.sub.3                                                                              OCH.sub.3                                       ##STR290##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR291##       H      CH.sub.3                                                                              OCH.sub.3                                       ##STR292##       H      CH.sub.3                                                                              OCH.sub.3                                       ##STR293##       H      CH.sub.3                                                                              CH.sub.3                                        ##STR294##       CH.sub.3                                                                              CH.sub.3                                                                              H                                               ##STR295##                                                                     ##STR296##       H      CH.sub.3                                                                              OCH.sub.3                                       ##STR297##       H      CH.sub.3                                                                              CH.sub. 3                                      ______________________________________                                    

    ______________________________________                                          ##STR298##                                                                    R       R.sup.1   R.sup.2 R.sup.3                                              ______________________________________                                         Cl      Cl        Cl      H                                                    F       Cl        Cl      H                                                    NO.sub.2                                                                               CF.sub.3  H       H                                                    Cl      CF.sub.3  H       COOH salts and esters                                Cl      Cl        H       H                                                    Cl      Cl        H       OCH.sub.3                                            Cl      Cl        H                                                                                       ##STR299##                                          H       CF.sub.3  Cl      OC.sub.2 H.sub.5                                     ______________________________________                                    

    ______________________________________                                          ##STR300##                                                                    R           R.sup.1             R.sup.2                                        ______________________________________                                         tert.-C.sub. 4 H.sub.9                                                                     NH.sub.2            SCH.sub.3                                      tert.-C.sub. 4 H.sub.9                                                                      ##STR301##         SCH.sub.3                                                   ##STR302##                                                        ______________________________________                                    

    ______________________________________                                          ##STR303##                                                                    R       R.sup.1            R.sup.2                                                                               R.sup.3                                      ______________________________________                                          ##STR304##                                                                            sec-C.sub. 4 H.sub.9                                                                              H      H                                            H       CH.sub.3           H      H salts, esters                              H       sec-C.sub. 4 H.sub.9                                                                              H      H salts, esters                               ##STR305##                                                                            tert.-C.sub. 4 H.sub.9                                                                            H      H                                                     ##STR306##                                                                     ##STR307##                                                            ______________________________________                                    

    ______________________________________                                          ##STR308##                                                                    R       R.sup.1    R.sup.2    X                                                ______________________________________                                         CH.sub.3                                                                               CH.sub.3   H          CH.sub.3OSO.sub.2 O                              CH.sub.3                                                                               CH.sub.3   Br         CH.sub.3OSO.sub.2 O                              CH.sub.3                                                                               CH.sub.3   CH.sub.3   CH.sub.3OSO.sub.2 O                               ##STR309##                                                                     ##STR310##                                                                    ______________________________________                                    

    __________________________________________________________________________      ##STR311##                                                                    R         R.sup.1  R.sup.2        R.sup.3                                      __________________________________________________________________________     H         n . C.sub.3 H.sub.7                                                                     CH.sub.2CHCH.sub.2                                                                            CH.sub.3                                     Na        n . C.sub.3 H.sub.7                                                                     CH.sub.2CHCH.sub.2                                                                            CH.sub.3                                      ##STR312##                                                                     ##STR313##                                                                     ##STR314##                                                                    __________________________________________________________________________

    ______________________________________                                          ##STR315##                                                                    R     R.sup.1 R.sup.2 R.sup.3 R.sup.4                                          ______________________________________                                         Cl    H       Cl      OCH.sub.3                                                                              H salts, esters, amides                          Cl    Cl      H       Cl      H . (CH.sub.3).sub.2 NH                          ______________________________________                                    

    ______________________________________                                          ##STR316##                                                                    R             R.sup.1                                                                               R.sup.2                                                   ______________________________________                                          ##STR317##   CH.sub.3                                                                              H salts, esters, amides                                    ##STR318##   H      H salts, esters, amides                                    ##STR319##   H      H salts, esters, amides                                   ______________________________________                                    

    ______________________________________                                          ##STR320##                                                                    R               R.sup.1                                                                               R.sup.2                                                 ______________________________________                                          ##STR321##     H      H salts, esters, amides                                  ##STR322##     CH.sub.3                                                                              H salts, esters, amides                                  ##STR323##     CH.sub.3                                                                              H salts, esters, amides                                 ______________________________________                                    

    ______________________________________                                          ##STR324##                                                                    R                         R.sup.1                                              ______________________________________                                          ##STR325##              H salts, esters, amides                                ##STR326##              H salts, esters, amides                                ##STR327##                                                                     ##STR328##                                                                     ##STR329##                                                                     ##STR330##                                                                     ##STR331##              salts, esters                                          ##STR332##                                                                     ##STR333##                                                                     ##STR334##              salts                                                  ##STR335##                                                                     ##STR336##              salts, esters, amides                                 ______________________________________                                    

It is also possible to apply the new compounds according to the invention, either alone or in combination with other herbicides, in admixture with further crop protection agents, e.g., agents for combatting pests, or phytopathogenic fungi or bacteria. Of further interest is the miscibility of the compounds with mineral salt solutions used to eliminate nutritional or trace element deficiencies.

Spreader-stickers are nonphytotoxic oils may be added to ensure the herbicidal action.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure as fine a distribution of the active ingredient as possible.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient. Application rates vary from 0.1 to 10, especially from 0.5 to 5, kg of active ingredient per hectare.

EXAMPLE 7

90 parts by weight of compound 1 is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 8

20 parts by weight of compound 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 9

20 parts by weight of compound 5 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 10

20 parts by weight of compound 6 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 11

20 parts by weight of compound 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

EXAMPLE 12

3 parts by weight of compound 2 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

EXAMPLE 13

30 parts by weight of compound 5 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

EXAMPLE 14

40 parts by weight of compound 6 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.04 wt% of active ingredient.

EXAMPLE 15

20 parts of compound 1 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained. 

We claim:
 1. A compound of the formula ##STR337## where R¹ is lower alkynyl; lower haloalkenyl; lower haloalkynyl; lower alkoxycarboalkyl; lower alkoxycarboalkenyl; lower alkanoylalkyl; lower azidoalkyl; lower thiocyanatoalkyl; lower cyanoalkyl; carbamyl-lower alkyl; carbamyl-lower alkyl substituted by halogen; halo- or methyl substituted phenyl; lower alkylmercaptoalkyl, lower phenylmercaptoalkyl, wherein in said alkylmercaptoalkyl and phenylmercaptoalkyl the final alkyl has more than 1 carbon atom; or methyl substituted by lower O-alkyl-N-alkylaminophosphorothio, lower O,O-dialkylphosphoro, lower O,O,O-trialkylphosphinylimino, lower alkoxy thiocarbonyl thio, lower alkylsulfinyl, thiocarbamido, isothiuronium hydrochloride, ##STR338## lower alkanoylamido, lower alkanoylamido substituted by halogen, phthalylimidoalkyl, isoxazole or isoxazole substituted by methyl or halogen;R² is isopropyl; n is 2; R and R³ are lower alkyl, R⁴ is lower alkyl or hydrogen, R⁵ is lower alkyl or phenyl; and each Y and Y' independently is oxygen or sulfur.
 2. 1-propargyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 3. 1-azidomethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 4. 1-thiocyanatomethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 5. 1-cyanomethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 6. 1-thiocarbamidomethyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 7. 1-methyl-(O-ethyl-N-isopropylaminophosphorothio)-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 8. 1-propargyl-3-sec-butyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide. 